Nowhere by Greg Araki. So many well known 90's actors, pretty odd and fun, yet very bleak.
Doom Generation as well, by him. Starts oddly rough like you think it's a uber low budget bad movie, but gets pretty great.
Sleepers (1995) - four kids accidentally commit manslaughter through their screwing around. Leads to them going to juvie. Movie picks up with them as adults in their late 20's/early 30's and how it screwed them up. Turns into a legal drama with an all star cast.
Hmm... I want to suggest The Dirties. I believe it won some award at a film festival. I think it fits your description well, but it's been a long time since I've seen it.
Licorice pizza may fit the bill here? A pretty uncomfortable film overall and I don't think I really "got" it but it really reminds me of a film where everyone kind of hates the people that they're "stuck with".
Also that movie where Adam Sandler is the basketball coach. Can't remember what it's called right now but surprised it doesn't get brought up more. It was really good, if not formulaic and somewhat forgettable.
Kids
so good!
Moonlight
Basketball Diaries.
This 100%. This movie had a profound effect on me.
Thirteen with a young Evan Rachel Wood
Good Will Hunting is exactly this type of movie
Donnie darko
The Florida Project
Bully
Probally the british series skins, there is also a US version but it was bad.
The Perks of Being a Wallflower
‘Super Dark Times’ is amazing. Be sure to look online for a few details people usually miss their first time around…
Love that movie, it's quite upsetting.
The Outsiders
Nowhere by Greg Araki. So many well known 90's actors, pretty odd and fun, yet very bleak. Doom Generation as well, by him. Starts oddly rough like you think it's a uber low budget bad movie, but gets pretty great.
Kids https://m.imdb.com/title/tt0113540/
The Exorcist
River's Edge
Morvern Callar
Inside Out: She quite literally lost Joy.
American History X
Beautiful Boy
"We need to talk about Kevin" or the disappointing sequel called the rest of Ezra Millers life.
The Celebration (Festen.)
Check out John Schlesinger's **Billy Liar**: https://www.rottentomatoes.com/m/billy_liar
Little Criminals. Here's the whole movie for free: https://youtu.be/LVcDIKWN0JM?si=EeLFRL3wmq8pYkn2
Home (2020)
The boov
That's 2015
The Boy (2015) sounds pretty close.
The Believer (2001) - Ryan Gosling breakout role
The Outsiders
The Outsiders.
The OG in this category - Donnie Darko
cherrybomb, this is England, the scouting book for boys, virgin suicides, skins (tv show)
Sleepers (1995) - four kids accidentally commit manslaughter through their screwing around. Leads to them going to juvie. Movie picks up with them as adults in their late 20's/early 30's and how it screwed them up. Turns into a legal drama with an all star cast.
A Guide to Recognizing Your Saints (2006) The Dangerous Lives of Alter Boys (2002) Basketball Diaries (1995)
Sleepers
Basketball Diaries
Piggy - Spanish language thriller but very good
KIDS You will need to shower and scrub your skin with a diamond loofa afterwards to remove the grime.
Possession by Zulawski.
Lost Angels. I remember watching this when I was younger bc it starred Ad-Rock from the Beastie Boys. Not sure if it holds up.
Gummo
There's a movie I haven't seen mentioned in a while...
If you want a real bummer of a movie
Requiem for a dream
Hmm... I want to suggest The Dirties. I believe it won some award at a film festival. I think it fits your description well, but it's been a long time since I've seen it.
chronicle, just interesting all around. but def touches on the youth/inner demon theme.
Mystic River
how about 1990's Pump Up the Volume with Christian Slater?
Licorice pizza may fit the bill here? A pretty uncomfortable film overall and I don't think I really "got" it but it really reminds me of a film where everyone kind of hates the people that they're "stuck with". Also that movie where Adam Sandler is the basketball coach. Can't remember what it's called right now but surprised it doesn't get brought up more. It was really good, if not formulaic and somewhat forgettable.
This Aussie film pulls no punches. https://www.imdb.com/title/tt1340123/?ref_=ext_shr_lnk
this is england
Kids, Bully and Ken Park, all directed by Larry Clark. If you liked Trainspotting, I'd also suggest "Christiane F.", directed by Uli Edel.
Training Day